P
US5280024AExpiredUtilityPatentIndex 91

Medicinal use of 3',5'-di-tert.-butyl-4'-hydroxy flavones

Assignee: ADIRPriority: Mar 31, 1992Filed: Mar 25, 1993Granted: Jan 18, 1994
Est. expiryMar 31, 2012(expired)· nominal 20-yr term from priority
Inventors:ROLLAND YVESLEWIN GUYVILAINE JEAN-PAULLENAERS ALBERTTHOLLON CATHERINE
C07D 405/12A61P 9/10A61P 9/08C07D 311/30
91
PatentIndex Score
32
Cited by
1
References
21
Claims

Abstract

Compounds of general formula (I): <IMAGE> in which R represents: - a hydrogen atom, or - a radical -OR' in which R' is as defined in the description. Medicaments.

Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A method for treating an animal or human living body afflicted with a disease, requiring an antioxidant and anti-vaso constrictor, resulting from a vascular tissue disorder related to the oxidation of biological structures, comprising the step of administering to the said body an effective amount of a compound selected from those of formula (I): ##STR23## in which: R represents: hydrogen or   a radical OR' in which R' represents: a) hydrogen   b) an alkyl radical containing 1 to 10 carbon atoms inclusive in a straight or branched chain optionally substituted by one or more substituents selected from the group consisting of: α) phenyl and monocyclic or bicyclic aromatic heterocyclic radicals, all optionally substituted by one or more substituents selected from halogen atoms and trifluoromethyl and hydroxy radicals and alkyl and alkoxy radicals each having 1 to 5 carbon atoms inclusive in a straight or branched chain,   β) carboxy,   γ) alkoxycarbonyl in which the alkoxy group contains 1 to 5 carbon atoms inclusive in a straight or branched chain,   δ) aminocarbonyl of the formula: ##STR24##  in which each of R' 1  and R' 2 , which may be identical or different, represent: hydrogen, or an alkyl radical having 1 to 5 carbon atoms inclusive in a straight or branched chain, or R' 1  and R' 2  form together with the nitrogen atom to which they are bonded a heterocyclic radical optionally containing a second hetero atom selected from oxygen, nitrogen and sulfur, which heterocyclic radical may be substituted by an alkyl radical having 1 to 5 carbon atoms inclusive in a straight or branched chain or by an aralkyl radical, the aryl moiety of which is optionally substituted by one or more alkyl and alkoxy radicals each having 1 to 5 carbon atoms inclusive in a straight or branched chain,   ε) an amino radical of the formula ##STR25##  in which each of R" 1  and R" 2 , which may be identical or different, represents:   hydrogen, or an alkyl or hydroxyalkyl radical each having 1 to 5 carbon atoms inclusive in a straight or branched chain, or   R" 1  and R" 2  form together with the nitrogen atom to which they are bonded a heterocycle optionally containing another hetero atom selected from oxygen, nitrogen, and sulfur,   ζ) a radical --OR" in which R" represents hydrogen, an alkyl radical having 1 to 5 carbon atoms inclusive in a straight or branched chain or a group --COA in which: A represents an alkyl radical having 1 to 5 carbon atoms inclusive in a straight or branched chain, or a radical ##STR26##  in which R" 1  and R" 2  are as defined above, and η) --SO 3  H or --SO 3  M in which M represents an alkali metal;     c) an acyl radical of the formula: --COR"' in which R"' represents: an alkyl radical having 1 to 10 carbon atoms inclusive in a straight or branched chain,   an aralkyl radical, the aryl moiety of which is optionally substituted by one or more substituents selected from halogen atoms and hydroxy radicals and alkyl and alkoxy radicals each having 1 to 5 carbon atoms inclusive in a straight or branched chain, or   an aryl radical optionally substituted in the same manner as the aryl moiety of the aralkyl radical defined above, in c) and     d) tosyl, their stereoisomers and also their possible addition salts with a pharmaceutically-acceptable acid or base.       
     
     
       2. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-7,4'-dihydroxyflavone. 
     
     
       3. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-7-n-hexyloxyflavone. 
     
     
       4. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-7-(4"-morpholinylethoxy) flavone. 
     
     
       5. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-p-chlorobenzyloxy flavone. 
     
     
       6. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-(2"-piperidino-2"-oxoethoxy)flavone. 
     
     
       7. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-[2"-(N-benzylpiperazino)-2"-oxo-ethoxy]flavone. 
     
     
       8. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-(N,N-diethylacetamidoxy) flavone. 
     
     
       9. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-(2"-quinolylmethoxy) flavone. 
     
     
       10. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-[2-(N,N-dimethylamino) ethoxy]flavone. 
     
     
       11. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-[3"-(N,N-dimethylamino) propoxy]flavone. 
     
     
       12. Method of claim 1 wherein the compound is Ethyl 5-[7-(3',5'-di-tert.-butyl-4'-hydroxy)flavone] oxyvalerate. 
     
     
       13. Method of claim 1 wherein the compound is 3-[7-(3',5'-di-tert.-butyl-4'-hydroxy)flavone] oxypropanesulfonic acid. 
     
     
       14. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-(2-hydroxyethoxy) flavone. 
     
     
       15. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxyflavone. 
     
     
       16. Method of claim 1 wherein the compound is Ethyl 2-[7-(3',5'-di-tert.-butyl-4'-hydroxy)flavone]oxy-2,2-dimethyl acetate. 
     
     
       17. Method of claim 1 wherein the compound is Ethyl 2-[7-(3',5'-di-tert.-butyl-4'-hydroxy)flavone] oxyacetate. 
     
     
       18. Method of claim 1 wherein the compound is 2-[7-(3',5'-di-tert.-butyl-4'-hydroxy)flavone]oxyacetic acid. 
     
     
       19. Method of claim 1 wherein the compound is Sodium 2-[7-(3',5'-di-tert.-butyl-4'-hydroxy)flavone] oxyacetate. 
     
     
       20. Method of claim 1 wherein the compound is Pentyl 2-[7-(3',5'-di-tert.-butyl-4'-hydroxy)flavone] oxyacetate. 
     
     
       21. Method of claim 1 wherein the compound is 3',5'-di-tert.-butyl-4'-hydroxy-7-(3",5"-di-tert.-butyl-4"-hydroxybenzoyloxy)flavone.

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